


Slow

by Sashataakheru



Category: Taskmaster (UK TV) RPF
Genre: Anal Play, Anal Sex, Community: seasonofkink, D/s, Daddy/boi, Dildos, Distractions, Edging, Enthusiastic Consent, Fingering, First Time, Kissing, M/M, Prepping, Spanking, Teasing, slow fuck
Language: English
Status: Completed
Published: 2018-08-23
Updated: 2018-08-23
Packaged: 2019-07-01 12:41:15
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,062
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15774327
Author URL: https://archiveofourown.org/users/Sashataakheru/pseuds/Sashataakheru
Summary: Greg is a good Daddy who introduces Alex to the delights of buttsex in the most agonisingly beautiful way possible.





	Slow

**Author's Note:**

> Written for the prompt 'anal play' for Season of Kink 2018. My card and fills are [here](https://3evilmuses.dreamwidth.org/82357.html).
> 
> Are you as surprised as me that it’s taken this long for me to write Greg and Alex actually having sex? Because I sure as shit am.

They’d spent a long time just kissing on Greg’s bed, getting to know each other. Greg was trying to teach him how to be a better kisser, too, but Alex wasn’t sure he was really improving. But he also knew it was a distraction from thinking about what Greg really wanted to do with him that night. He was anxious about having sex with him for the first time, and Greg was doing his best to calm him down and get him into it.  
  
It started slowly. Greg didn’t want to rush him. He was just stroking him, caressing him, gently running his hands down his thighs, making him feel good before he went any further. He pulled Alex on top of him and distracted him with kisses while his hands began caressing his cheeks, and lightly spanking them. Alex found that helped, weirdly, though he didn’t really know why. He knew he liked spanking, but that was about as far as he’d got. But even those few light spanks told him Greg would be very good at it, and that thrilled him.  
  
Greg’s hands felt so big as they stretched him and massaged him and spanked him. He didn’t really know half of what he was doing or why, but it felt good. He did want to have sex with him, it was just that this was just all new to him, and he had no idea how it would feel. And all the while, Greg kept kissing him, holding him close as he warmed him up.  
  
“I’m gonna start with a finger, yeah? I’ll go slow, I promise. Let me know if I need to stop. We don’t need to fuck tonight if you’re not ready,” Greg said.  
  
“Alright, I know, thank you, sir,” Alex said, trying not to get nervous.  
  
Alex expected to feel it straight away. Instead, there was lube, and his finger just gently rubbing the area, getting him used to that sensation. It did feel nice, though, and Greg moved slowly, just probing him gently, moving in a little further each time, just so he could get used to it.  
  
“How’s that feel, boy? Does that feel good?” Greg asked.  
  
Alex thought a moment as Greg began moving his finger in and out, just slowly, while his other hand kneaded his cheek. It did feel good. He hadn’t known if it would feel good to him, but it did. That his cock was getting hard helped relax him, and reassured him that this was pleasurable.  
  
“I like it, yes, sir,” Alex said.  
  
“Do you want me to continue? Do you want another finger?” Greg said.  
  
“Not yet, let me get used to this first. Maybe in a bit, sir,” Alex said.  
  
“Alright, in a while. You know I love preparing a new sub for the first time. I love showing them how amazing their butts are when they’re in the hands of someone who knows what they’re doing. I love watching them discover all this wonderful new pleasure for themselves, it’s so delightful to watch. Long ago, someone taught me all these things, when I was in your position, and now I get to teach them to you, and see how they make you feel the way I did back then. We’ve all been new subs, new bottoms, at one point in our lives. Yes, it can be a bit scary, but it doesn’t have to be. It’s wonderful, and I want to be the one to show you how wonderful it can really be,” Greg said, unable to help murmuring in his ear, knowing Alex liked the sound of his voice like that.  
  
Alex shivered, but his words did help. “Were you anxious too, sir? Did it hurt, sir?”  
  
“I was a bit anxious, yeah, but I felt more discomfort than pain. My top prepared me well, and it didn’t last. If you’re relaxed, if you’re in the mood, it shouldn’t hurt, because your body wants it. And that’s a wonderful place to be. I know you want it, don’t you, Alex? Trust me, I won’t hurt you,” Greg said.  
  
Alex did want it. He’d had too many fantasies about being fucked by him to not want to sleep with him. It was all just now very real, and he needed time to get used to that. It did feel good though. It still felt good, and he trusted Greg to take care of him.  
  
“Maybe add another one now, please, sir?” Alex said after a while.  
  
“Alright, but let me know if we need to stop. This might feel weird,” Greg said.  
  
It did feel weird, if Alex was honest, but it also felt better than he imagined it would. It’s not like Greg had tiny hands, so perhaps he was being stretched more than he might otherwise be, but Greg moved slowly, getting him used to two, and the more he did it, the more Alex grew to enjoy it.  
  
“Oh, I did not expect that to feel so good already. What are you doing, sir?” Alex said.  
  
“I’m taking it slow, and you’re relaxing into it. I can feel it. That’s good, I want you to enjoy it. I’ve got a few toys we can play with, too, if you like, if you want to get used to something bigger before you take my cock. And if we don’t get there tonight, that’s fine. I still got to play with your butt and make you feel good, and that’s enough for me,” Greg said. “There’ll always be another night.”  
  
“T-toys? What kind of toys, sir?” Alex said, both unsure and aroused at the idea.  
  
“I mean, you’re probably not up for the anal beads at the moment, but there’s a couple of dildos you might enjoy. I’ll introduce you to butt plugs later,” Greg said.  
  
“Show me, sir?” Alex said, curious.  
  
“Alright, stay there for a moment,” Greg said.  
  
Alex moved off him and waited for Greg to return, and seeing them for the first time, he wasn’t sure they would actually fit inside him at all. They looked too big, surely.  
  
“Do you want to try one on me? I quite like this one,” Greg said, offering him one of the dildos.  
  
“O-on you, sir? Are you sure, sir?” Alex said, taking it, unsure what on earth he was meant to do with it.  
  
“Yeah, I’m sure. Just lube it up and I’ll show you how to insert it. And how to fuck me with it,” Greg said, lying down on his stomach.  
  
“I-I, no, I don’t really know what I’m doing, sir. Maybe – maybe later, sir?” Alex said, giving the dildo back to him.  
  
“Alright, fair enough. Maybe later. Lie down, on your front, then. I’ll keep working you some more,” Greg said.  
  
“Yes, sir.”  
  
Alex obeyed, pulling a pillow under his chest to help support his arms. Greg moved between his legs, and the fingers were back, slowly thrusting inside him, and it helped him relax. There was a moment, too, when he felt his cock just rest on him, clearly ready to go, but he didn’t attempt to fuck him, he was just getting him used to it being there, to give him a sense of what it felt like. And Alex had to admit, the sensation of feeling the tip of his master’s cock just brushing over his anus was incredible. Ever so slightly he pushed at it, not aiming to penetrate, just to tease.  
  
Then the fingers were back, this time working just so slightly to stretch him and open him up. Alex allowed himself to relax into it, getting used to his master’s hands teasing him like this.  
  
“I’m going to add another finger, boy, I just want to stretch you some more. Is that alright? Are you ready for that?” Greg said.  
  
“Yes, sir, I’m ready for that, sir,” Alex said, pleasantly surprised to realise how much he did want it.  
  
Alex still chewed his lip as his master pushed his fingers in again, this time three, and it did feel different. Not in a bad way, but just different. The stretching this time was more intense, but not unpleasant. He could feel his master kissing his cheeks, spanking him, kneading him, teasing him relentlessly to the point where all his anxieties disappeared. He was definitely aware of how turned on he was, which he found reassuring. The last thing he wanted was to finally get the master of his dreams, only to find out he couldn’t deal with the physicality of it at all. But his fears had been misplaced, and he was very much getting into this.  
  
“Alright, hands and knees, boy, I just want to try one of the dildos first, just to see if you’re ready yet,” Greg said.  
  
“Yes, sir.”  
  
Alex obeyed, and felt rather more exposed than he had before, but his master spanked his arse a few times, stretched him, kneaded his cheeks, and began teasing him with a dildo, one that felt smaller than he was expecting.  
  
“I’m just going to push it in a little bit. Tell me if it hurts,” Greg said.  
  
“Yes, sir, I will, sir,” Alex said.  
  
Alex braced himself, but it didn’t hurt at all. He felt stretched, but because he couldn’t see what his master was doing, it was too easy to pretend it was his master’s cock, and that just made him hard, thinking about how much he wanted it.  
  
“Is that okay?” Greg asked.  
  
“It feels good, sir, thank you, sir,” Alex said.  
  
“I’ll move it in a bit more, get you used to what a cock feels like inside you. I know so much of this is new to you, and I don’t want you to freak out about it, yeah? Some boys need a bit of time to get used to how a cock feels inside them before they’re ready for sex, and there’s nothing wrong with that,” Greg said.  
  
“Yes, sir, I appreciate it, sir, thank you, sir,” Alex said.  
  
The sensation of the dildo slowly pushing inside him actually felt wonderful. He wasn’t expecting that. He wasn’t sure what he thought it would feel like, but it did feel good. It also felt strange, to feel so stretched and full, but not in a bad way. And then, Greg pulled it out just as slowly, and Alex gasped, not expecting _that_ to feel good, either.  
  
“Oh, god, sir,” Alex couldn’t help saying as his master pushed it in again.  
  
“Yeah, do you like that, boy? Should I just fuck you with this tonight? I don’t know, maybe you’re not ready for my cock just yet,” Greg said.  
  
“Whatever you feel is right for me, sir,” Alex said, deciding either option meant he’d get fucked one way or another, and that was perfectly fine with him.  
  
Greg kept slowly thrusting with the dildo, using his other hand to stroke Alex’s cock. Alex noticed he was slowly speeding up, and he wondered what it would feel like if it were his master instead. Everything just felt amazing, and he didn’t really know why. Every now and then, he spanked him, or he rubbed his back, or he fondled his balls, and he had not been prepared for how good it would all feel.  
  
“Would you like to feel my cock inside you yet? Or aren’t you ready? It’s okay to not be ready yet,” Greg said.  
  
“I-I think I would like that, sir, yes please, sir,” Alex said.  
  
“Alright, but if it’s too much, please tell me to stop. You don’t have to continue if you don’t feel comfortable with it. I might be your master, but I’m not here to force you to have sex with me. It’s not an obligation. It should be something you want to do with me, alright? Do you understand?” Greg said.  
  
“Yes, sir, I do, sir. I understand. At least let me feel you inside me once. Then I will decide if I want to continue, sir,” Alex said.  
  
“As you wish, boy,” Greg said.  
  
Greg teased him some more with the dildo, just to make sure he was prepared enough for him, before he slowly removed it and prepared to push his cock in for the first time. There was a bit more lube and a rubber, a few more spanks, and he rubbed his back gently, before he slowly began to enter him. Alex flinched a little, and Greg pulled out.  
  
“Is it hurting, Alex? Tell me if I need to stop,” Greg said.  
  
“N-no, it’s fine, sir, I was just – surprised. It feels so strange, but it doesn’t hurt, sir,” Alex said.  
  
“Do you want me to continue?” Greg asked.  
  
“Yes, please, sir,” Alex said.  
  
“You sure? You’re not just saying that to please me? Because I don’t fuck boys who do that. You need to be into it, too,” Greg said.  
  
“Yes, I really want it, sir, please continue, sir,” Alex said.  
  
“Alright, I’ll keep going,” Greg said.  
  
Alex didn’t flinch this time, and allowed his master to slowly push in again. This time, he was ready, and it felt good. His master’s cock was inside him, and he felt amazing.  
  
“There, that’s just the head. Does that feel alright?” Greg asked.  
  
“That’s your cock, sir? Oh, it feels better than I ever thought it would, sir,” Alex said. He felt stretched, but in a good way, thankful for his master fucking him with the dildo, so he didn’t find it so strange when he entered him.  
  
“Shall I continue?” Greg asked.  
  
“Yes, please, sir,” Alex said.  
  
Greg moved in a little further, and Alex gasped. He almost wanted him to move faster because the slowness of it was driving him crazy. The dildo had felt fairly solid, but nothing like the real thing. The real thing felt so much better.  
  
“Please, more, sir, please, I need you, sir,” Alex said.  
  
“See, you just take it slow, and everything’s fine, isn’t that right, boy? I’ll see how much of me you can take,” Greg said.  
  
Alex breathed in as Greg continued to push slowly inside him, his hands holding his hips firmly. And when Greg was in as far as Alex could take, he slowly began to pull out, and Alex was sure he lost his mind at that point.  
  
“Oh, please, god, more please, sir,” Alex begged.  
  
Greg pushed in again, a little faster. “Still feeling good, boy?”  
  
“Yes, sir, more than I can say, sir,” Alex said.  
  
“Good, good. I knew you’d enjoy it,” Greg said. “I’ll start slow, and maybe I’ll stay slow and draw this out all night, before you feel what it’s like when a man comes inside you. You’d like that, wouldn’t you, boy? You’d like your daddy to fuck you all night until he comes inside you?” Greg said.  
  
“I would like that very much, sir, yes please, sir,” Alex said, unable to begin to imagine what that would feel like. He knew what it was like to do that with a woman, but he had no idea what it would be like to have his master come inside him, and he wanted desperately to find out.  
  
Greg slowly began thrusting, taking his time, getting Alex used to the movements as much as he was teasing the ever-loving shit out of him by dragging it out as long as possible. Alex was making these adorable little whimpers, filled with desperation, but Greg wasn’t going to give in. He’d got him this far, and he wasn’t about to rush to the end just yet.  
  
“You’d better hold on for me, boy, I don’t want you coming before I’m ready,” Greg said.  
  
“Y-yes, sir, I’ll try my best, sir,” Alex said, distracted again by Greg pushing in.  
  
“You feel really good, boy. I’m going to enjoy edging you all night. That sweet release will drive you mad when I let you come at last,” Greg said.  
  
Alex didn’t doubt it for a moment. “Yes, sir, thank you, sir.”  
  
Alex couldn’t tell how long it lasted. His master fucked him slowly, teased him badly, kept stopping him from coming until he was ready, and Alex was so frustrated by it all. He’d never been so turned on and denied so much pleasure, and he was beginning to realise just how good his master was, and how little experience he really had. He’d learnt so much tonight already, and they’d just barely begun.  
  
Greg really only sped up, just a little bit, towards the end, when Alex was on the verge of frustrated tears, as his master teased him some more before denying him again. He knew the moment his master had come as he grabbed his hips and pulled him close, and the sounds he made almost threatened to wreck him but he held on with what little willpower he had left, not willing to ruin things for his master now. He desperately wanted his master to make him come now, but he held on, and the feeling of his master lingering, just a little, as he wrapped his arms around him were unlike anything he’d ever experienced before. His master slapped his thigh as he pulled out, and Alex turned to look at him, praying for relief.  
  
“On your back. Let me reward you for being such a good boy,” Greg said.  
  
“Yes, sir,” Alex said.  
  
Alex didn’t waste any time obeying, and could only look at him with wide eyes as his master went down on him, his fingers slipping up his butt again. Alex held on tight, but he didn’t last long, nor did he feel his master wanted him to, and he was sure he’d never felt pleasure like it before in his life. It overwhelmed him completely, and his master kept using his mouth on him, caressing him with his hands, rubbing him down, making it all last just that little bit longer.  
  
Eventually, Greg brought him into his arms and kissed him, and all Alex wanted to do was stay here forever, just stay in his arms and let him bring him pleasure over and over again. Greg whispered to him, murmured praise against his skin, and Alex just listened to it and let peace settle over him. He had no words left, not anymore.


End file.
